Isolation, Semi-Synthesis, and Nmr Spectral Studies of Loline Alkaloids

Petroski, Richard J.; Yates, Scott R.; Weisleder, David; Powell, Richard G.

doi:10.1021/np50064a023

Cited by 60 publications

(58 citation statements)

References 11 publications

(31 reference statements)

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“…Lolines 2, 4 and 5 can then be separated on a silica gel column eluted with 5-20% MeOH in CHCl 3 , and 1 can be purified from 2 on a neutral alumina column eluted with 2% MeOH in CHCl 3 (Petroski et al, 1989). Lolines can also be separated by paper chromatography or TLC on silica gel or alumina plates Robbins et al, 1972;TePaske et al, 1993a,b;Yates, 1963;Yates et al, 1990;Yates and Tookey, 1965).…”

Section: Methods For Isolation and Analysis Of Lolinesmentioning

confidence: 99%

Loline alkaloids: Currencies of mutualism

et al. 2007

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Section: Methods For Isolation and Analysis Of Lolinesmentioning

confidence: 99%

Loline alkaloids: Currencies of mutualism

et al. 2007

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“…These alkaloids have an unusual structure, comduced by a pathway involving polyamines such as spermiprising a saturated 1-aminopyrrolizidine-ring system, dine. However, results of precursor feeding studies have with a highly strained ether bridge between C-2 and C-7 now ruled out this possibility and suggest that lolines (Petroski et al 1989). Lolines are almost exclusively are formed by a novel biosynthetic pathway from the amino acids l-proline and l-homoserine (Blankenship et al 2005).…”

mentioning

confidence: 99%

Gene Clusters for Insecticidal Loline Alkaloids in the Grass-Endophytic Fungus Neotyphodium uncinatum

et al. 2005

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Loline alkaloids are produced by mutualistic fungi symbiotic with grasses, and they protect the host plants from insects. Here we identify in the fungal symbiont, Neotyphodium uncinatum, two homologous gene clusters (LOL-1 and LOL-2) associated with loline-alkaloid production. Nine genes were identified in a 25-kb region of LOL-1 and designated (in order) lolF-1, lolC-1, lolD-1, lolO-1, lolA-1, lolU-1, lolP-1, lolT-1, and lolE-1. LOL-2 contained the homologs lolC-2 through lolE-2 in the same order and orientation. Also identified was lolF-2, but its possible linkage with either cluster was undetermined. Most lol genes were regulated in N. uncinatum and N. coenophialum, and all were expressed concomitantly with loline-alkaloid biosynthesis. A lolC-2 RNA-interference (RNAi) construct was introduced into N. uncinatum, and in two independent transformants, RNAi significantly decreased lolC expression (P Ͻ 0.01) and loline-alkaloid accumulation in culture (P Ͻ 0.001) compared to vector-only controls, indicating involvement of lolC in biosynthesis of lolines. The predicted LolU protein has a DNA-binding site signature, and the relationships of other lol -gene products indicate that the pathway has evolved from various different primary and secondary biosynthesis pathways.

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“…Briefly, dried herbage (0.5 g) was shaken vigorously with 10 ml of dichloromethane: methanol: ammonia (75: 25: 0.5) solvent and 6 mg phenylmorphine (PM) per 100 ml of solvent as the internal standard, for 24 h. After centrifugation at 2000g for 15 min, 1 ml of the supernatant was taken up in a 1 ml plastic syringe and passed through a micro-filter (0.45 mm) into a glass gas chromatograph (GC) vial for loline alkaloid analyses within 24 h. Extraction, purification of loline dihydrogen chloride and derivatisation to NFL, NAL, N-methyl loline (NML) and N-acetyl norloline (NANL) was based on the methods of Petroski et al (1989) and Blankenship et al (2001) modified by Patchett et al (2011). Loline alkaloid concentrations were calculated as mg/g DM of root biomass.…”

Section: Loline Analysismentioning

confidence: 99%

Effects of loline-producing endophyte-infected meadow fescue ecotypes on New Zealand grass grub (Costelytra zealandica)

Patchett

Gooneratne

Chapman³

et al. 2011

New Zealand Journal of Agricultural Research

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Loline alkaloids produced by endophyte-infected meadow fescue were high (!1000 mg/g) in roots. The larvae of New Zealand grass grub are major subterranean pasture pests. In laboratory and field studies, grass grub larvae feeding on roots of endophyte-infected meadow fescue containing lolines at concentrations !450 mg/g either lost weight or gained less weight than the corresponding controls feeding on endophyte-free or low-loline meadow fescue. These results demonstrate that loline alkaloids in roots of meadow fescue have the potential to deter grass grub larvae from feeding and could contribute to control of this pest in a sustainable manner.

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Isolation, Semi-Synthesis, and Nmr Spectral Studies of Loline Alkaloids

Cited by 60 publications

References 11 publications

Loline alkaloids: Currencies of mutualism

Loline alkaloids: Currencies of mutualism

Gene Clusters for Insecticidal Loline Alkaloids in the Grass-Endophytic Fungus Neotyphodium uncinatum

Effects of loline-producing endophyte-infected meadow fescue ecotypes on New Zealand grass grub (Costelytra zealandica)

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